The present invention relates to N-substituted triorganostannylhydrocarbylcarboxylic acid hydrazides useful as insecticides.
Various substituted organotin compounds are known to be useful as pesticides, acaricides, bactericides, fungicides, herbicides or protective coatings.
U.S. Pat. No. 3,976,672 discloses (hydrocarbylphenylsulfonyl)alkyltrimethylstannanes. Although these compounds exhibit insecticidal properties they are generally too phytotoxic to be used on a crop such as cotton.
U.S. Pat. No. 3,538,088 relates to preparations for combatting molluscs (snails, insect larvae) containing as active substance a compound of the general formula (R.sub.1)(R.sub.2)(R.sub.3)SnX.sub.1 CX.sub.2 YNR.sub.4 R.sub.5, wherein R.sub.1, R.sub.2 and R.sub.3 are phenyl or substituted phenyl, and X.sub.1 and X.sub.2 are sulfur and/or oxygen.
U.S. Pat. No. 3,520,910 discloses organosubstituted tin aminocarbamates of the formula (R).sub.2 R'SnNRCOONX useful as catalysts for curing silicone rubbers and preparing urethane foams.
German Patent Publications Nos. 2,558,163 and 2,554,790 disclose tetrasubstituted tin compounds of the formula (CH.sub.3).sub.3 Sn(CH.sub.2).sub.n CR'H-X as herbicides and pesticides. One of those compounds is (CH.sub.3).sub.3 SnCH.sub.2 CH.sub.2 CONHNH.sub.2, 3-trimethylstannylpropionic acid hydrazide, which is the starting compound for the synthesis of many of the compounds of the present invention. It appears as Compound 148 in Table I below. Compound 148 and many compounds of the present invention may also be named as derivatives of propanoic acid rather than of propionic acid. In naming many compounds of the present invention, a comma is often inserted between the words "acid" and "hydrazide".
The compounds of the present invention possess unusually good insecticidal properties, especially against the order Lepidoptera. The larval stages of Heliothis virescens (tobacco budworm) and Heliothis zea (cotton bollworm) cause considerable damage to cotton. The compounds of this invention are distinguished from prior art organotin compounds proposed for insect control because they exhibit high efficacy at low rates of application, with little or no phytotoxicity.